ORGANIC CHEMISTRY. Wiley STUDY GUIDE AND SOLUTIONS MANUAL TO ACCOMPANY ROBERT G. JOHNSON JON ANTILLA ELEVENTH EDITION. University of South Florida
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1 STUDY GUIDE AND SOLUTIONS MANUAL TO ACCOMPANY ORGANIC CHEMISTRY ELEVENTH EDITION T. W. GRAHAM SOLOMONS University of South Florida CRAIG B. FRYHLE Pacific Lutheran University SCOTT A. SNYDER Columbia University ROBERT G. JOHNSON Xavier University JON ANTILLA University of South Florida Wiley
2 CONTENTS To the Student INTRODUCTION "Solving the Puzzle" or "Structure Is Everything (Almost)" xi xiii CHAPTER 1 THE BASICS: BONDING AND MOLECULAR STRUCTURE 1 Solutions to Problems 1 15 CHAPTER 2 FAMILIES OF CARBON COMPOUNDS: FUNCTIONAL GROUPS, INTERMOLECULAR FORCES, AND INFRARED (IR) SPECTROSCOPY 18 Solutions to Problems CHAPTER 3 ACIDS AND BASES: AN INTRODUCTION TO ORGANIC REACTIONS AND THEIR MECHANISMS 34 Solutions to Problems CHAPTER 4 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 46 Solutions to Problems CHAPTER 5 STEREOCHEMISTRY: CHIRAL MOLECULES 65 Solutions to Problems vi
3 CONTENTS vii CHAPTER 6 IONIC REACTIONS-NUCLEOPHILIC SUBSTITUTION AND ELIMINATION REACTIONS OF ALKYL HALIDES 85 Solutions to Problems CHAPTER 7 ALKENES AND ALKYNES I: PROPERTIES AND SYNTHESIS. ELIMINATION REACTIONS OF ALKYL HALIDES 106 Solutions to Problems CHAPTER 8 ALKENES AND ALKYNES II: ADDITION REACTIONS 130 Solutions to Problems CHAPTER 9 NUCLEAR MAGNETIC RESONANCE AND MASS SPECTROMETRY: TOOLS FOR STRUCTURE DETERMINATION 157 Solutions to Problems CHAPTER 10 RADICAL REACTIONS 182 Solutions to Problems CHAPTER 11 ALCOHOLS AND ETHERS 203 Solutions to Problems
4 viii CONTENTS CHAPTER 12 ALCOHOLS FROM CARBONYL COMPOUNDS: OXIDATION- REDUCTION AND ORGANOMETALLIC COMPOUNDS 227 Solutions to Problems ANSWERS TO FIRST REVIEW PROBLEM SET 259 (First Review Problem Set is available only in WileyPlus, CHAPTER 13 CONJUGATED UNSATURATED SYSTEMS 278 Solutions to Problems SUMMARY OF REACTIONS BY TYPE, CHAPTERS METHODS FOR FUNCTIONAL GROUP PREPARATION, CHAPTERS CHAPTER 14 AROMATIC COMPOUNDS 308 Solutions to Problems CHAPTER 15 REACTIONS OF AROMATIC COMPOUNDS 325 Solutions to Problems CHAPTER 16 ALDEHYDES AND KETONES. NUCLEOPHILIC ADDITION TO THE CARBONYL GROUP 357 Solutions to Problems
5 CONTENTS ix CHAPTER 17 CARBOXYLIC ACIDS AND THEIR DERIVATIVES: NUCLEOPHILIC ADDITION-ELIMINATION AT THE ACYL CARBON Solutions to Problems CHAPTER 18 REACTIONS AT THE a CARBON OF CARBONYL COMPOUNDS: ENOLS AND ENOLATES Solutions to Problems CHAPTER 19 CONDENSATION AND CONJUGATE ADDITION REACTIONS OF CARBONYL COMPOUNDS: MORE CHEMISTRY OF ENOLATES 448 Solutions to Problems CHAPTER 20 AMINES 488 Solutions to Problems CHAPTER 21 PHENOLS AND ARYL HALIDES: NUCLEOPHILIC AROMATIC SUBSTITUTION 530 Solutions to Problems ANSWERS TO SECOND REVIEW PROBLEM SET 550 (Second Review Problem Set is available only in WileyPlus, CHAPTER 22 CARBOHYDRATES 566 Solutions to Problems
6 x CONTENTS CHAPTER 23 LIPIDS 596 Solutions to Problems CHAPTER 24 AMINO ACIDS AND PROTEINS 610 Solutions to Problems CHAPTER 25 NUCLEIC ACIDS AND PROTEIN SYNTHESIS 626 Solutions to Problems 626 Special Topics A-F and H are available only in WileyPlus, Solutions to problems in the Special Topics are found on the following pages: Special Topic A 13 C NMR Spectroscopy 634 Special Topic B Chain-Growth Polymers 636 Special Topic C Step-Growth Polymers 637 Special Topic D Thiols, Sulfur Ylides, and Disulfides 643 Special Topic E Thiol Esters and Lipid Biosynthesis 645 Special Topic F Alkaloids 646 Special Topic G Carbon Carbon Bond-Forming and Other Reactions of Transition Metal Organometallic Compounds 651 Special Topic H Electrocyclic and Cycloaddition Reactions 654 APPENDIX A EMPIRICAL AND MOLECULAR FORMULAS 659 Problems 661 Additional Problems 662 Solutions to Problems of Appendix A 663 APPENDIX B ANSWERS TO QUIZZES 667 APPENDIX C MOLECULAR MODEL SET EXERCISES 682
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